I live in Salem but I keep my boat in Maine so I've never sailed here and can't tell you much. I don't think there will be much, if any, ice in the harbor. Pretty sure I've seen some boats in the water at one of the marinas at Pickering Wharf. There is a water taxi service that provides moorings and transport to and from your boat:

Unless there are extreme temps in the winter for multiple days, ice is not an issue. The incoming/outcoming tides keep the harbor free.

In the winter, there are no water taxi services during the winter. Last Water Taxi services stop Nov 1 and don't start until April 30.

There is free public parking (overnight), first come, first serve in Marblehead (Village St), but not during the winter. They also pull the docks in the winter, so even if you do have a dingy, access is tough.

I don't know about the Salem side, parking wise, but I am thinking no, since Salem doesn't have many egress points unless you go through Hawthorne Cove or Pickering Wharf marinas and they are private/members only.

The harbor is "crowded", but it is also one of the larger ones in New England. It is nowhere near as tightly packed as Marblehead harbor or Rockport for example.

"S" - From the Kernwood Bridge to the Beverly Bridge in the Danvers River is designated Area "S". There is a long waiting list and very little turnover.

"A" - From the Beverly Bridge to Monument Bar is designated Area "A". There is very little space here and poor access from shore. This area is predominantly used by two Yacht Clubs, the Jubilee and Salem Willows.

"L" - From Monument Bar to Winter Island Light is designated Area "L". There is space available but poor access and exposure to severe weather.

"WI" - From Winter Island Light to the Power Plant Jetty is designated Area "WI". There is available space and good access from Winter Island Park. The Park Dept charges non-residents an entrance fee to the park. Launch service is now available at Winter Island for 2006 season. Parking pass and launch service for $500 per year. Call Hawthorne Cove Marina for details at 978-740-9890 or Winter Island Park at 978-745-9430.

"E" - From the Power Plant Jetty to Derby Wharf Light is designated Area "E". There is very little available space and poor public access here.

"M" - From Derby Light to Forest River is designated Area "M". There is room in this area but the water is shallow and access poor.

Rental's:
Rental moorings are available through Hawthorne Cove Marina and Salem Water Taxi. All are located in area E. Both provide launch service with your mooring. The approx. price is $1000. per year.
Pickering Wharf Marina and Hawthorne Cove Marina also have slips available. The approx price is $125. per foot for the length of the boat.

Jubilee Yacht Club is reasonable and nice if you want to go around the point to Beverly.

Winter Island charges in the summer for parking, not the winter though.

Brewer Hawthorne Cove Marina is shallow. Max draft is 6-6.5 feet at MLW. Similar at Pickering. Pickering Wharf is also tight quarters for maneuvering

Salem side of harbor is more exposed. Aside from Pickering Wharf area, best spot for calm in a Nor'easter is on the Marblehead side near the Waterside cemetery. Naugus Head/Point Protects it well. As NaviGsr states: Near Salem Power plant, it's a coal burning plant, lots of soot on your boat.

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